Showing my age here, but [Fallout Boy's 2003 debut album] Take This to Your Grave is still one of the most influential albums of my music life.
It's interesting that you're coming from a perspective where an album this "young" can feel aged.
I heard something on the radio recently that some survey or another was taken, and that on average, people's musical interest ossifies at age 33. Obviously, there is a lot of indidivual variation. But I know it happened to me early -- everything post-grunge feels brand new to me. Mid-1990s stuff falls into the exact same mental bucket as an act that comes out tomorrow.
That can get in the way of appreciation often, but thankfully not 100% of the time.
Interesting. For me it's more a matter of growing up, changing tastes, and changing friends. I started getting really "into music" in the late 90s with a handful of close friends. From ~99-06 or so, high school thru early college, a very close friend and I were so into it, mostly the hip-hop and pop punk/ska scenes of the time, lots of shows, sharing music, CDs, filesharing sites, all that. He ended up dropping out of college in the summer of 2005 and our relationship deteriorated (he was into drugs, I distanced myself from him and his friends, lots of backstory there that I'll skip). I listened to very little new music between like 2006 and 2009 and then got back into it on my own late in college with the help of this forum.
So there's like a window in there that is my mental stopping point. I look back on the music I listened to back then and can't help but cringe sometimes especially with the cheesy emo punk, but there's nothing to be ashamed of. I'd be lying if I said I didn't still listen to it at times, and I can still hear a lot of similarities in the music I listened to back in the day with newer stuff.
I wish we were more into the "classics", so to speak. My repertoire is almost nonexistent on music prior to 1980 and pretty thin from 1980-mid 90s other than a decent amount of new wave/shoegaze. Maybe that should be my next goal.